Electrooxidation-induced selective cleavage of C-N bonds of tertiary amines to access thioureas, selenoureas, and 2-aminated benzoselenazoles

A metal-free, operationally simple, and scalable electrooxidation-induced selective cleavage of C-N bonds of tertiary amines to access asymmetric thiourea, selenourea, and 2-aminated benzoselenazole derivatives is reported. More than 50 examples were reported and were obtained in greater than 96% yield. Importantly, the readily accessible compounds 10c (12.6%, 10.36%) and 24c (6.45% +/- 1.40) possess promising anticancer activity against the mouse breast cancer cell line and the human lung adenocarcinoma cancer cell line (A549), reiterating the importance of the developed methodology.

Automated summary

A metal-free, operationally simple, and scalable electrooxidation method was reported for the selective cleavage of C-N bonds of tertiary amines, providing access to asymmetric thiourea, selenourea, and 2-aminated benzoselenazole derivatives. Over 50 examples were reported with yields greater than 96%. The readily accessible compounds 10c and 24c showed promising anticancer activity against mouse breast cancer and human lung adenocarcinoma cancer cell lines (A549), highlighting the importance of this methodology.